Hydrogen Peroxide → 4-Propylpicolinonitrile

HRID 1269087Notes

Reaction equation

HRID 1269087 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)[CH2:2][CH3:3].OO.C[Si]([C:16]#[N:17])(C)C.CN(C)C(Cl)=O>C(=O)([O-])[O-].[K+].[K+]>[CH2:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:16]#[N:17])[CH:5]=1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 6598Dimethylcarbamoyl ChlorideHCID 707384-PropylpyridineHCID 82115Trimethylsilyl cyanide

Product 1

HCID 230032234-PropylpicolinonitrileYield 93%

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent

Procedure

To 4-propylpyridine (2.5 g, 20 mmol), 30% hydrogen peroxide (2.4 g) was added and refluxed overnight. The solvent was removed and the resulting residue was taken in DCM (30 mL). Trimethylsilyl cyanide (2.6 g, 26 mmol) was added to the above solution followed by dimethylcarbamyl chloride (2.8 g, 26 mmol), and the reaction mixture was stirred at rt overnight. Potassium carbonate (10%, 100 mL) was added. The organic layer was separated, dried over sodium sulfate and then concentrated to obtain 4-propyl-2-cyanopyridine (2.5 g, 93%). The crude nitrile was dissolved in aqueous hydrochloric acid (6N, 60 mL) and refluxed overnight. The 4-propyl-2-carboxylic acid pyridine 10b (R9=propyl) was obtained after crystallization from acetonitrile (2 g, 71%).

Workup

  1. temperaturerefluxed overnight
  2. customThe solvent was removed
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4d4a836c52ee4dcb88681a2a18e35bb3
Source dataset
uspto-grants-2007_04
Patent number
US07199105B2

Reaction notes

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